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Check prices for these dates

Next weekend
4 Rab. II - 6 Rab. II
In two weeks
11 Rab. II - 13 Rab. II
In one month
25 Rab. II - 27 Rab. II
In two months
23 Jum. I - 25 Jum. I

Compare 91 Cottages in Chester with updated reviews, rates, and availability.

Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
Property grounds

Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands

9.8 out of 10, Exceptional, (108)
"Awesome "
The price is SAR 671
SAR 979 total
includes taxes & fees
2 Apr - 3 Apr
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
Charming Cottage in the Heart of the Shawangunks
Fridge, oven, stovetop, coffee/tea maker

Charming Cottage in the Heart of the Shawangunks

10.0 out of 10, Exceptional, (7)
"My bridesmaids and I stayed here the night before my wedding and my husband and I the night of my wedding ..it is absolutely beautiful and private just what we wanted! Would definitely stay here again!"
The price is SAR 938
SAR 1,984 total
includes taxes & fees
6 Apr - 7 Apr
Charming Cottage in the Heart of the Shawangunks
Chestnut - Charming 3-bedroom cottage in wonderful Fishkill!
Property grounds

Chestnut - Charming 3-bedroom cottage in wonderful Fishkill!

Chestnut - Charming 3-bedroom cottage in wonderful Fishkill!
Hello Small Stone
Exterior

Hello Small Stone

9.6 out of 10, Exceptional, (4)
"The house has a lot of character and the outdoor areas are really peaceful. The owner just needs to resolve the issue with sulfur in the water because the rotten egg smell is too strong to tolerate."
The price is SAR 675
SAR 1,118 total
includes taxes & fees
9 Apr - 10 Apr
Hello Small Stone
Fenced Yard Private Lakes 7 Beaches Huge Fire Pit
Lake

Fenced Yard Private Lakes 7 Beaches Huge Fire Pit

9.8 out of 10, Exceptional, (98)
"Great Highland Lakes Cottage! Clean & well stocked kitchen. Be careful going up or down Breakneck Rd. Thus time of year every view is beautiful! We did lots of small road trips taking in the sites and autumnal views!!"
Fenced Yard Private Lakes 7 Beaches Huge Fire Pit
A romantic cottage and artist's retreat looking down over an enchanted lake
Property grounds

A romantic cottage and artist's retreat looking down over an enchanted lake

9.4 out of 10, Exceptional, (96)
"It was an awesome stay we loved the couple days we got to spend there!!"
A romantic cottage and artist's retreat looking down over an enchanted lake
Cottage at Millpond Falls - Romantic Luxury Escape - Waterfall views in Warwick
Pool

Cottage at Millpond Falls - Romantic Luxury Escape - Waterfall views in Warwick

10.0 out of 10, Exceptional, (142)
"Such a beautiful location. The cottage is quant while having all the modern updates. The hosts have carefully left an array of coffee and welcome goodies, including fresh eggs from their ducks. Will be back! "
Cottage at Millpond Falls - Romantic Luxury Escape - Waterfall views in Warwick
Historic 1800's Cornwall-On-Hudson Cottage!
Outdoor dining

Historic 1800's Cornwall-On-Hudson Cottage!

10.0 out of 10, Exceptional, (22)
"Best VRBO OUR FAMILY HAS RENTED .ABSOLUTELY PERFECT, THOUGHTFUL AND SUPER CLEAN,"
Historic 1800's Cornwall-On-Hudson Cottage!
Putnam Valley Vacation Rental: Patio & Lake Views!
Cottage (3 Bedrooms) | Private kitchen | Microwave, oven, stovetop, blender

Putnam Valley Vacation Rental: Patio & Lake Views!

3.0 star property
Putnam Valley Vacation Rental: Patio & Lake Views!
Beautiful Cottage in Hudson Valley w/Pool & Views
Smart TV, fireplace

Beautiful Cottage in Hudson Valley w/Pool & Views

10.0 out of 10, Exceptional, (11)
"The house was beautifully decorated and furnished well. We enjoyed the large kitchen. The host responded to questions quickly and well. It is a beautiful region. Views were lovely, and roads and driveway were scraped of snow before we had time to think about it. "
The price is SAR 934
SAR 2,389 total
includes taxes & fees
31 Mar - 1 Apr
Beautiful Cottage in Hudson Valley w/Pool & Views
Luxe 10 guest Cottage Ski/Golf/Fire Pit/Lakes/Hike
Property grounds

Luxe 10 guest Cottage Ski/Golf/Fire Pit/Lakes/Hike

2.0 star property
8.0 out of 10, Very Good, (2)
"Nice"
The price is SAR 938
SAR 1,926 total
includes taxes & fees
7 Apr - 8 Apr
Luxe 10 guest Cottage Ski/Golf/Fire Pit/Lakes/Hike
Relaxing Farm Cottage Escape, 10 Min from LEGOLAND
Terrace/patio

Relaxing Farm Cottage Escape, 10 Min from LEGOLAND

9.8 out of 10, Exceptional, (9)
"We had a great stay in this cozy cabin! The beds were comfortable and the views of the farm and deer were beautiful ! Communication with Ginny was quick and she let us adjust our dates of stay when needed. 😊"
The price is SAR 619
SAR 1,168 total
includes taxes & fees
31 Mar - 1 Apr
Relaxing Farm Cottage Escape, 10 Min from LEGOLAND
Charming Lake Community Cottage 2BR Retreat Near Mountain Creek
Fridge, microwave, oven, stovetop

Charming Lake Community Cottage 2BR Retreat Near Mountain Creek

10.0 out of 10, Exceptional, (1)
"We recently stayed here for the first time in order to visit with our new grandbaby nearby. It far exceeded our expectations - absolutely charming, two good sized bedrooms, working fireplace!, lovely living space, clean, clean, clean, parking spot, anything you forgot (toothbrush, etc.) provided, and a free snack basket! We'll be back. Communication with the host was immediate and helpful. Easy check-in and check-out. Ten stars."
Charming Lake Community Cottage 2BR Retreat Near Mountain Creek
Mountain House Escape - 1 Hour from NYC
Outdoor pool

Mountain House Escape - 1 Hour from NYC

10.0 out of 10, Exceptional, (7)
"We recently had the pleasure of staying at Deer Hill in Warwick, NY, and it truly exceeded our expectations. The property is set on three-acre expanse in a lovely, and ultra-quiet neighborhood. It was an ideal home for our annual family gathering, which includes our 3 adult children, spouses and two young grandchildren. The large in-ground pool was a hit, and was a source of fun and relaxation throughout our stay. The pool has a shallow end and an 8-foot deep end. The spacious great room served...
Mountain House Escape - 1 Hour from NYC
Cozy Haven: A Romantic Retreat in our Tiny House!
Living area

Cozy Haven: A Romantic Retreat in our Tiny House!

7.0 out of 10, Good, (9)
"we enjoyed the cozy home it is a nice place to get away"
The price is SAR 563
SAR 994 total
includes taxes & fees
31 Mar - 1 Apr
Cozy Haven: A Romantic Retreat in our Tiny House!
Dreamy Hudson Valley Cottage w/ State Park Views
TV, fireplace, books

Dreamy Hudson Valley Cottage w/ State Park Views

9.8 out of 10, Exceptional, (12)
"We loved our two nights at this perfect, comfortable cottage in the Garrison woods. Communication with Ashley was terrific, very prompt and welcoming. The house was very clean and we had a great view. Thank you for a great stay! "
Dreamy Hudson Valley Cottage w/ State Park Views
Putnam Valley Vacation Rental: Patio & Lake Views!
Fridge, microwave, stovetop, coffee/tea maker

Putnam Valley Vacation Rental: Patio & Lake Views!

9.8 out of 10, Exceptional, (12)
"Stayed for a couple of nights whilst visiting our daughter….. greedy place. Thanks "
Putnam Valley Vacation Rental: Patio & Lake Views!
Hickory - Charming 3-bedroom cottage in serene Fishkill!
Property grounds

Hickory - Charming 3-bedroom cottage in serene Fishkill!

Hickory - Charming 3-bedroom cottage in serene Fishkill!
Lakefront Getaway : Mountain & Lakes views
Outdoor dining

Lakefront Getaway : Mountain & Lakes views

10.0 out of 10, Exceptional, (4)
"The property is beautiful and relaxing, exactly what we needed. The house is cozy with full amenities needed if you were staying longer than just a few nights."
Lakefront Getaway : Mountain & Lakes views
NEW Spacious 5 bedrooms with Public Lake & Beach Access and Kayak!
Exterior

NEW Spacious 5 bedrooms with Public Lake & Beach Access and Kayak!

10.0 out of 10, Exceptional, (5)
"The house is even more beautiful than the photos. From the spa-like bathrooms, to toys and books for kids, to the little extra amenities like qtips and bandaids, it was the perfect getaway for everyone in our party of all ages."
NEW Spacious 5 bedrooms with Public Lake & Beach Access and Kayak!
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Other property types in Chester

Private Estate 9BR w/Pool, Hot Tub & Scenic Views!
Interior

Private Estate 9BR w/Pool, Hot Tub & Scenic Views!

Private Estate 9BR w/Pool, Hot Tub & Scenic Views!
Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo
Outdoor dining

Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo

9.6 out of 10, Exceptional, (5)
"Plenty of room for my family"
The price is SAR 972
SAR 1,092 total
includes taxes & fees
31 Mar - 1 Apr
Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
Property grounds

Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands

9.8 out of 10, Exceptional, (108)
"Awesome "
The price is SAR 671
SAR 979 total
includes taxes & fees
2 Apr - 3 Apr
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Frequently asked questions

How much do cottages in Chester cost?
Prices for cottages in Chester range between SAR 563 and SAR 938 per night. Whatever your budget, you’re sure to find an ideal place to get in tune with nature. These prices were available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.
Why book your cottage in Chester with Expedia?
Booking a cottage in Chester is as simple as deciding on your travel dates and choosing your ideal place for a vacation in nature. From chic retreats to affordable stays and cottages that include conveniences like a kitchen, Expedia has something for all tastes and styles. As for the best deals around? We’ve have them as well!
How can I find cheap cottages in Chester?
With Expedia’s useful filter tool, scoring cheap cottages in Chester is a snap. To find properties that’ll make your hip pocket happy, refine your search by amenities, star rating and budget.